EP2103604A1 - Procédé de fabrication d'épichlorhydrine - Google Patents
Procédé de fabrication d'épichlorhydrine Download PDFInfo
- Publication number
- EP2103604A1 EP2103604A1 EP08102653A EP08102653A EP2103604A1 EP 2103604 A1 EP2103604 A1 EP 2103604A1 EP 08102653 A EP08102653 A EP 08102653A EP 08102653 A EP08102653 A EP 08102653A EP 2103604 A1 EP2103604 A1 EP 2103604A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- mixture
- allyl chloride
- hydrogen peroxide
- chloropropane
- reaction
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims description 36
- 238000004519 manufacturing process Methods 0.000 title description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims abstract description 109
- 239000000203 mixture Substances 0.000 claims abstract description 72
- OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 claims abstract description 71
- SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 claims abstract description 29
- 239000003054 catalyst Substances 0.000 claims abstract description 24
- ULYZAYCEDJDHCC-UHFFFAOYSA-N isopropyl chloride Chemical compound CC(C)Cl ULYZAYCEDJDHCC-UHFFFAOYSA-N 0.000 claims abstract description 21
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims abstract description 20
- 239000011541 reaction mixture Substances 0.000 claims abstract description 20
- 239000010936 titanium Substances 0.000 claims abstract description 20
- 229910052719 titanium Inorganic materials 0.000 claims abstract description 20
- 238000004821 distillation Methods 0.000 claims abstract description 18
- 239000010457 zeolite Substances 0.000 claims abstract description 17
- 229910021536 Zeolite Inorganic materials 0.000 claims abstract description 16
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 238000006243 chemical reaction Methods 0.000 claims description 64
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 24
- 239000002904 solvent Substances 0.000 claims description 9
- 238000000066 reactive distillation Methods 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 150000001336 alkenes Chemical class 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 238000006735 epoxidation reaction Methods 0.000 description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- -1 Glycol ethers Chemical class 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000006735 deficit Effects 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 230000000717 retained effect Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- FGUUSXIOTUKUDN-IBGZPJMESA-N C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 Chemical compound C1(=CC=CC=C1)N1C2=C(NC([C@H](C1)NC=1OC(=NN=1)C1=CC=CC=C1)=O)C=CC=C2 FGUUSXIOTUKUDN-IBGZPJMESA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 229910010413 TiO 2 Inorganic materials 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 description 1
- 150000004056 anthraquinones Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000008119 colloidal silica Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 125000005624 silicic acid group Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D301/00—Preparation of oxiranes
- C07D301/02—Synthesis of the oxirane ring
- C07D301/03—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds
- C07D301/12—Synthesis of the oxirane ring by oxidation of unsaturated compounds, or of mixtures of unsaturated and saturated compounds with hydrogen peroxide or inorganic peroxides or peracids
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/10—Process efficiency
Definitions
- the invention relates to a process for the preparation of epichlorohydrin by reacting allyl chloride with hydrogen peroxide.
- Epichlorohydrin Chlormethyloxiran
- z. B. is used for the production of resins.
- a suitable process for the preparation of epichlorohydrin is the EP-A 0 100 119 known reaction of allyl chloride with hydrogen peroxide in the presence of a titanium-containing zeolite catalyst.
- allyl chloride In order to obtain a high selectivity for epichlorohydrin in this reaction, allyl chloride must be used in stoichiometric excess to hydrogen peroxide, such as from WO 2004/043941 is known. Unreacted allyl chloride can be separated by distillation and recycled to the epoxidation reaction, such as. B. off WO 02/00634 or WO 02/14298 is known.
- the two chloropropanes can therefore be removed by distillation of allyl chloride only with great effort. If the reaction of allyl chloride with hydrogen peroxide, a technical, chloride-contaminated allyl chloride is used and unreacted allyl chloride separated by distillation and in the Epoxidation reaction is attributed, it is therefore an enrichment of chloropropanes in the process.
- a method according to the invention in which, in a first reaction stage, a chloropropane-containing allyl chloride is reacted in excess with hydrogen peroxide.
- the unreacted allyl chloride is separated and recycled to the reaction wherein a portion of the separated allyl chloride is fed to a second reaction stage and reacted with hydrogen peroxide, the amount of hydrogen peroxide in the second reaction stage being selected to substantially and preferably substantially fully react the allyl chloride , From the reaction mixture of the second reaction stage, the chloropropanes can then be separated by distillation without losses of allyl chloride.
- allyl chloride and hydrogen peroxide are reacted in the presence of a titanium-containing zeolite catalyst to form epichlorohydrin.
- the allyl chloride used contains 1-chloropropane and / or 2-chloropropane.
- Technical grades of allyl chloride which contain 1-chloropropane and / or 2-chloropropane as by-products of the industrial production of allyl chloride can therefore be used for the process according to the invention.
- the content of 1-chloropropane and 2-chloropropane in the allyl chloride used is preferably in the range of 0.01 to 2 wt .-%, particularly vorzut in the range of 0.05 to 0.8 wt .-%.
- Hydrogen peroxide can be used as an aqueous solution, which preferably has a content of hydrogen peroxide in the range from 1 to 90% by weight, particularly preferably from 10 to 80% by weight and in particular from 30 to 70% by weight. Hydrogen peroxide can be used as a commercially available, stabilized solution. Also suitable is the non-stabilized hydrogen peroxide prepared by the anthraquinone process, which can be used without further purification.
- an off WO 2004/028962 known hydrogen peroxide uses less than 50 ppm alkali metals and alkaline earth metals, less than 50 ppm bases having a pK B of less than 4.5 and at least 100 ppm anions, each based on the weight of hydrogen peroxide.
- a solution of hydrogen peroxide in methanol is used, which was preferably prepared by reacting hydrogen and oxygen over a palladium catalyst in methanol.
- a hydrogen peroxide solution in methanol according to claim 9 of WO 2006/108784 used is particularly preferred, the 2 to 15 wt .-% hydrogen peroxide, 0.5 to 20 wt .-% water, 60 to 95 Wt .-% methanol, 10 -6 to 10 -2 mol / l bromide, and 10 -6 to 0.1 mol / l dimethyl sulfate and / or monomethyl sulfate.
- titanium-containing zeolite catalyst it is possible to use all titanium-containing zeolites known from the prior art which have a catalytic activity for the reaction of olefins with hydrogen peroxide.
- the titanium-containing zeolite catalyst used is preferably a titanium silicalite having an MFI or MEL crystal structure. Particular preference is given to using titanium silicalites of the composition (TiO 2 ) x (SiO 2 ) 1-x , where x is in the range from 0.001 to 0.05. Most preferred are titanium silicalites which are prepared by the process according to WO 01/64581 or the method according to WO 01/64582 were manufactured.
- the titanium-containing zeolite catalyst can be used in the novel process in the form of a suspension catalyst.
- the reaction is preferably carried out so that the catalyst suspended in the reaction mixture is retained in the first reaction stage, for example by filtration or by sedimentation, so that the reaction mixture which is separated in a distillation in step b) contains no catalyst ,
- the titanium-containing zeolite catalyst is used in the process of the invention in the form of a fixed bed catalyst.
- Particularly suitable are extrusion-formed fixed-bed catalysts in the form of extrudates having a diameter of 1 to 5 mm, preferably a binder in an amount of 1 to 99 wt .-%, particularly preferably 1 to 40 wt .-%, based on the titanium-containing Contain zeolite.
- All the binders which react under the reaction conditions neither with the hydrogen peroxide used nor with the epichlorohydrin formed are suitable.
- Particularly suitable binders are silicic acids.
- fixed bed catalysts in which a fumed silica, a colloidal silica sol or a tetraalkyl orthosilicate or a combination of two of these components have been used as precursors for the binder.
- fixed bed catalysts which are based on the WO 01/72419 known methods were prepared by molding a molding composition having a plateau value of the Curd curve in the range of 20 to 90 mm.
- step a) in the first reaction stage allyl chloride and hydrogen peroxide are reacted in a molar ratio of allyl chloride to hydrogen peroxide in the range from 1.5: 1 to 5: 1.
- the molar ratio of allyl chloride to hydrogen peroxide is 2: 1 to 4: 1.
- the selectivity for epichlorohydrin decreases in the first reaction stage.
- Higher molar ratios have the disadvantage that large amounts of unreacted allyl chloride must be separated and recycled with a corresponding expenditure of energy.
- step d) of the process according to the invention in the second reaction stage, allyl chloride and hydrogen peroxide are reacted in a molar ratio of allyl chloride to hydrogen peroxide in the range from 0.5: 1 to 1.25: 1.
- the molar ratio of allyl chloride to hydrogen peroxide is 0.8: 1 to 1.15: 1.
- the use of a molar ratio in these ranges makes it possible to fully or largely convert allyl chloride in the second reaction stage, so that the mixture (C) obtained in step e) and removed from the process in step f) only uses a small proportion of the compound used Allyl chloride contains.
- the reaction of allyl chloride and hydrogen peroxide is carried out in steps a) and d), preferably in the presence of a solvent.
- a solvent Particularly suitable Solvents which dissolve under the reaction conditions allyl chloride and hydrogen peroxide and do not or only to a small extent with hydrogen peroxide or epichlorohydrin.
- Suitable solvents include, for example, alcohols, such as methanol, ethanol or tert-butanol; Glycols such as ethylene glycol, 1,2-propanediol or 1,3-propanediol; cyclic ethers, such as tetrahydrofuran or dioxane; Glycol ethers such as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, ethylene glycol monobutyl ether or propylene glycol monomethyl ether; and ketones such as acetone or 2-butanone.
- Preferred solvents are aliphatic alcohols having 1 to 4 carbon atoms. Most preferably, methanol is used as the solvent.
- the proportion of solvent in the reaction mixture in the first reaction stage is preferably 10 to 95 wt .-%, particularly preferably 30 to 80 wt .-% and in the second reaction stage, preferably 10 to 95 wt .-%, particularly preferably 30 to 80 wt .-%.
- the reaction of allyl chloride and hydrogen peroxide is carried out in the first reaction stage preferably at a temperature in the range of 0 ° C to 100 ° C, more preferably 30 ° C to 65 ° C and in the second reaction stage, preferably at a temperature in the range of 0 ° C. to 100 ° C, more preferably 30 ° C to 65 ° C.
- the pressure in the reaction stages can be freely chosen within wide limits and is preferably chosen so high that the boiling point of allyl chloride at the pressure used is equal to or higher than the reaction temperature used.
- the reaction conditions are preferably chosen in the first reaction stage so that a conversion of hydrogen peroxide in the range of 50% to 100%, preferably from 80% to 99.8%, is achieved.
- the reaction conditions are preferably chosen so that of the components Allyl chloride and hydrogen peroxide used in the molar deficit component to 70% to 100%, preferably to 90% to 99%.
- the reaction in steps a) and d) is carried out continuously in a fixed bed reactor, wherein a mixture containing hydrogen peroxide, optionally solvent and allyl chloride or the mixture (A2) is passed over a fixed bed of the titanium-containing zeolite catalyst.
- the fixed-bed reactor used is preferably a tubular reactor cooled from the outside, in particular a tube-bundle reactor.
- the fixed bed reactor can be operated in both upflow and downflow, with downflow operation in the trickle bed state being preferred.
- the reaction can be carried out in two or more reactors connected in series.
- two reactors connected in series are used.
- two or more reactors arranged in parallel can be used, so that a reactor for catalyst regeneration can be taken out of operation and the reaction can be continued in a reactor connected in parallel.
- the reaction mixture formed in the first reaction stage is separated in step b) of the process according to the invention in a distillation into a mixture (A) containing unreacted allyl chloride, and 1-chloropropane and / or 2-chloropropane and a Mixture (B) containing epichlorohydrin.
- the distillation is preferably carried out as a continuous rectification, wherein a rectification column is fed in a middle section of the reaction mixture formed in the first reaction stage, at the top of the column, the mixture (A) is removed and from the bottom of the column, the mixture (B) is removed ,
- a rectification column with 10 to 50 theoretical plates is used.
- the rectification is preferably carried out at a pressure at the top of the column in the range of 0.2 to 3 bar and preferably at a reflux ratio of 0.5 to 5.
- the distillation is preferably conducted so that the resulting mixture (A) contains more than 95% of the allyl chloride contained in the feed reaction mixture and the resulting mixture (B) contains more than 95% of the epichlorohydrin contained in the feed reaction mixture.
- step c) of the process according to the invention the mixture (A) is divided into a mixture (A1) which is recycled to the first reaction stage and a mixture (A2) which is fed to the second reaction stage.
- the mixture (A) is divided so that 50% to 98%, more preferably 70% to 95% of the allyl chloride contained in the mixture (A) with the mixture (A1) is recycled to the first reaction stage.
- the mixture (A) is separated by distillation, so that the chloropropanes contained in mixture (A) are enriched in the mixture (A2).
- step e) of the process according to the invention the reaction mixture formed in the second reaction stage is separated in a distillation into a mixture (C), which 1-chloropropane and / or 2-chloropropane and a mixture (D) containing epichlorohydrin.
- the distillation is preferably carried out as a continuous rectification, wherein a rectification column is fed in a middle section of the reaction mixture formed in the second reaction stage, at the top of the column mixture (C) is removed and from the bottom of the column, the mixture (D) is removed ,
- a rectification column with 10 to 50 theoretical plates is used.
- the rectification is preferably carried out at a pressure at the top of the column in the range of 0.5 to 3 bar and preferably at a reflux ratio of 0.5 to 5.
- the distillation is preferably operated so that the resulting mixture (C) contains more than 90% of the chloropropanes contained in the feed reaction mixture and the resulting mixture (D) contains more than 95% of the epichlorohydrin contained in the feed reaction mixture.
- the mixture (D) obtained in step e) of the process according to the invention is recycled to the first reaction stage.
- This embodiment is particularly advantageous if hydrogen peroxide is used in molar excess in step d) and the mixture (D) still contains unreacted hydrogen peroxide. By returning to the first reaction stage, this unreacted hydrogen peroxide can still be used for the epoxidation of further allyl chloride.
- the first reaction stage is carried out in two series-connected reactors and the mixture (D) is recycled to the second reactor.
- steps d) and e) of the process according to the invention take place simultaneously in the form of a reactive distillation.
- the titanium-containing zeolite catalyst of the second reaction stage is disposed in a reaction section of a rectification column, the mixture (A2) is fed to the column at a point below the reaction section, and hydrogen peroxide is supplied at a point above the reaction section.
- the mixture (C) is removed and from the bottom of the column, the mixture (D) is removed.
Priority Applications (15)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08102653A EP2103604A1 (fr) | 2008-03-17 | 2008-03-17 | Procédé de fabrication d'épichlorhydrine |
| ES08873464T ES2379311T3 (es) | 2008-03-17 | 2008-12-16 | Procedimiento para la preparación de epiclorhidrina |
| RU2010142287/04A RU2456279C2 (ru) | 2008-03-17 | 2008-12-16 | Способ получения эпихлоргидрина |
| CN2008801281503A CN101983192B (zh) | 2008-03-17 | 2008-12-16 | 表氯醇制备方法 |
| JP2011500055A JP5615797B2 (ja) | 2008-03-17 | 2008-12-16 | エピクロロヒドリンの製造方法 |
| EP08873464A EP2285791B1 (fr) | 2008-03-17 | 2008-12-16 | Procédé de fabrication d'épichlorhydrine |
| AU2008353129A AU2008353129B2 (en) | 2008-03-17 | 2008-12-16 | Method for the production of epichlorohydrin |
| AT08873464T ATE548361T1 (de) | 2008-03-17 | 2008-12-16 | Verfahren zur herstellung von epichlorhydrin |
| PCT/EP2008/067584 WO2009115152A1 (fr) | 2008-03-17 | 2008-12-16 | Procédé de fabrication d'épichlorhydrine |
| US12/919,637 US8481765B2 (en) | 2008-03-17 | 2008-12-16 | Method for the production of epichlorohydrin |
| PL08873464T PL2285791T3 (pl) | 2008-03-17 | 2008-12-16 | Sposób wytwarzania epichlorohydryny |
| KR1020107020833A KR20100124300A (ko) | 2008-03-17 | 2008-12-16 | 에피클로로하이드린의 생산방법 |
| BRPI0822343-2A BRPI0822343A2 (pt) | 2008-03-17 | 2008-12-16 | Processo para a preparação de epicloroídrina |
| TW098108061A TWI427072B (zh) | 2008-03-17 | 2009-03-12 | 製備３－氯－１，２－環氧丙烷之方法 |
| HK11105877.4A HK1152034A1 (en) | 2008-03-17 | 2011-06-10 | Method for the production of epichlorohydrin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08102653A EP2103604A1 (fr) | 2008-03-17 | 2008-03-17 | Procédé de fabrication d'épichlorhydrine |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP2103604A1 true EP2103604A1 (fr) | 2009-09-23 |
Family
ID=39495151
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP08102653A Withdrawn EP2103604A1 (fr) | 2008-03-17 | 2008-03-17 | Procédé de fabrication d'épichlorhydrine |
| EP08873464A Not-in-force EP2285791B1 (fr) | 2008-03-17 | 2008-12-16 | Procédé de fabrication d'épichlorhydrine |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP08873464A Not-in-force EP2285791B1 (fr) | 2008-03-17 | 2008-12-16 | Procédé de fabrication d'épichlorhydrine |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8481765B2 (fr) |
| EP (2) | EP2103604A1 (fr) |
| JP (1) | JP5615797B2 (fr) |
| KR (1) | KR20100124300A (fr) |
| CN (1) | CN101983192B (fr) |
| AT (1) | ATE548361T1 (fr) |
| AU (1) | AU2008353129B2 (fr) |
| BR (1) | BRPI0822343A2 (fr) |
| ES (1) | ES2379311T3 (fr) |
| HK (1) | HK1152034A1 (fr) |
| PL (1) | PL2285791T3 (fr) |
| RU (1) | RU2456279C2 (fr) |
| TW (1) | TWI427072B (fr) |
| WO (1) | WO2009115152A1 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2149570A1 (fr) * | 2008-08-01 | 2010-02-03 | Hexion Specialty Chemicals Research Belgium S.A. | Procédé de fabrication d'épichlorhydrine avec peroxyde d'hydrogène et un complexe manganèse |
| EP2149569A1 (fr) * | 2008-08-01 | 2010-02-03 | Hexion Specialty Chemicals Research Belgium S.A. | Procédé de fabrication d'un 1,2-epoxyde |
| EP2354131A1 (fr) | 2010-02-02 | 2011-08-10 | Momentive Specialty Chemicals Research Belgium | Procédé de fabrication de 1,2-époxyde et dispositif pour effectuer ce procédé |
| EP2796452A1 (fr) | 2013-04-23 | 2014-10-29 | Momentive Specialty Chemicals Research Belgium S.A. | Procédé d' élimination de 1,2-époxy-5-hexène d'épichlorhydrine |
| RU2593205C1 (ru) * | 2015-06-10 | 2016-08-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Чувашский государственный университет имени И.Н. Ульянова" | Способ выделения концентрированного эпихлоргидрина из продуктов эпоксидирования хлористого аллила пероксидом водорода на титансодержащем цеолитном катализаторе |
| CN111574481A (zh) * | 2020-05-29 | 2020-08-25 | 中国科学院理化技术研究所 | 一种制备环氧氯丙烷的方法 |
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2008
- 2008-03-17 EP EP08102653A patent/EP2103604A1/fr not_active Withdrawn
- 2008-12-16 US US12/919,637 patent/US8481765B2/en not_active Expired - Fee Related
- 2008-12-16 CN CN2008801281503A patent/CN101983192B/zh not_active Expired - Fee Related
- 2008-12-16 KR KR1020107020833A patent/KR20100124300A/ko not_active Application Discontinuation
- 2008-12-16 EP EP08873464A patent/EP2285791B1/fr not_active Not-in-force
- 2008-12-16 JP JP2011500055A patent/JP5615797B2/ja not_active Expired - Fee Related
- 2008-12-16 PL PL08873464T patent/PL2285791T3/pl unknown
- 2008-12-16 AU AU2008353129A patent/AU2008353129B2/en not_active Ceased
- 2008-12-16 BR BRPI0822343-2A patent/BRPI0822343A2/pt not_active Application Discontinuation
- 2008-12-16 RU RU2010142287/04A patent/RU2456279C2/ru not_active IP Right Cessation
- 2008-12-16 AT AT08873464T patent/ATE548361T1/de active
- 2008-12-16 ES ES08873464T patent/ES2379311T3/es active Active
- 2008-12-16 WO PCT/EP2008/067584 patent/WO2009115152A1/fr active Application Filing
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- 2009-03-12 TW TW098108061A patent/TWI427072B/zh not_active IP Right Cessation
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Also Published As
| Publication number | Publication date |
|---|---|
| EP2285791A1 (fr) | 2011-02-23 |
| AU2008353129A1 (en) | 2009-09-24 |
| CN101983192B (zh) | 2013-04-03 |
| EP2285791B1 (fr) | 2012-03-07 |
| HK1152034A1 (en) | 2012-02-17 |
| TWI427072B (zh) | 2014-02-21 |
| JP2011515350A (ja) | 2011-05-19 |
| AU2008353129B2 (en) | 2012-06-28 |
| JP5615797B2 (ja) | 2014-10-29 |
| BRPI0822343A2 (pt) | 2015-06-16 |
| PL2285791T3 (pl) | 2012-07-31 |
| US8481765B2 (en) | 2013-07-09 |
| CN101983192A (zh) | 2011-03-02 |
| RU2010142287A (ru) | 2012-04-27 |
| KR20100124300A (ko) | 2010-11-26 |
| WO2009115152A1 (fr) | 2009-09-24 |
| ES2379311T3 (es) | 2012-04-24 |
| TW200951116A (en) | 2009-12-16 |
| US20110054197A1 (en) | 2011-03-03 |
| ATE548361T1 (de) | 2012-03-15 |
| RU2456279C2 (ru) | 2012-07-20 |
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